Dressing Up Long Shorts

Happy Friday, ladies. Today’s ootd is a twist on casual you may not have considered. I’m that woman who struggles to wear very sporty looks and takes every opportunity to dress up. That’s partly why wearing shorts is a challenge for me. When a  reader pointed out that these shorts aren’t much different than wearing a skirt (except for the slip) I decided to play with the look and settled on a blazer and shorts outfit. My rounds straw bag is a vintage Kate Spade and I have never seen one even close to it.


Today, I’m dressing those long white shorts you saw here, with a blazer and some metallic flats. It’s a look that could take you out to dinner, to a graduation,  a baby shower, or even a wedding shower. A blazer and shorts may not be on your style radar but it feels just right on mine.


woman standing in front of fence wearing linen blazer with shorts with gold ballet flats


This long linen blazer is the same shape as my beloved white one but in a gorgeous shade of aqua. It’s funny, but this one is called a long linen blazer but its actual length is 1/2″ shorter than my classic linen blazer. Go figure. This just reinforces for me that the name on a garment isn’t always indicative of what it really is. It comes in misses, petite, plus, and plus petite sizes 2-18. I’m wearing a 6 regular and think it runs true to size.




The jacket sleeves are the right length for me but I scrunched them up to add a bit of balance with the shorts. A bracelet might have been nice but it bordered on overkill so I left bare legs and forearms. The short column of white under the blazer feels more put together than if I had three colors in this look plus the shorts might look overpowered.


blonde woman wearing a blazer with shorts outfit plus metallic shoes


I needed a shoe that could elevate the look of this outfit, but my wedges felt too high (such a bad pun:) so I opted for these metallic flats. I love a great metallic shoe or bag because they’re a universal neutral. They’re a bit dressy but not too much because the style is so simple.



sideways view of blonde woman wearing aqua blazer with gold shoes

These are called platinum but look closer to gold than silver. They’re the newest color of my favorite ballet flats. They come in 13 colors, in sizes 3-14. Their working drawstring means you can adjust the fit according to your foot. I loosen the left one to better accommodate the bunion on that foot. They’re very soft Italian leather, but I still wear mine around the house for several hours to loosen them up. That way they’re sort of broken in, before I head out for a full day on my feet.



I went with simple silver earrings and a chain necklace ( I added the coin) because it feels more casual than gold. If you remove the blazer and swapped the flats for white tennies, you’d have a simple tee and shorts for running errands.

Have you worn a blazer with shorts? I keep trying to find skorts that aren’t too short for me, so if you have a brand you recommend, please drop it in the comment section.

4 over 50 fashion bloggers

The Over 50 Style Team is chatting LIVE today on Instagram at 11 am PT/2 pm PT. This week we are tackling skincare. What we’ve tried, love, and swear-by to keep our skin in tip-top shape. I hope you’ll join us here.

Thanks for reading ladies and remember to wear what makes you feel confident.


This post may contain affiliate links which won’t change your price but will share some commission.


  1. RoseAg
    June 13, 2021 / 10:53 am

    If you have the right place to go in this outfit I think it would look good.
    Plenty of big buildings in Southern climates have the A/C going full blast and if you’re someplace with a vent blowing right over you, as often happens to me, you’ll like the blazer.
    I like the comparison of long shorts to a skirt. So if you’d put a sweater or a blazer over your favorite twill straight skirt you could just as well be putting it over these shorts.

  2. Canadian Elizabeth
    June 13, 2021 / 7:25 am

    Absolutely perfect outfit with the right proportions and the colours make you sparkle! I don’t know what season those colours match, but they certainly are the best on you, Jennifer.

  3. Janet
    June 11, 2021 / 6:04 pm

    In southwestern Ontario we get some hot days but there are lots of cool ones too and most nights cool off. I was just saying I haven’t worn blazers for ages due to COVID and I’d love to wear them again, so I’m digging out the less business- like ones and styling them with jeans, skorts and shorts. Thanks for the inspiration. You look great as always.

    I hope the dental work is over soon.

  4. Kathy
    June 11, 2021 / 4:51 pm

    I have found the skorts at Talbots are a good length. I’m 5’2 and wear the regular size for the length instead of my usual petite. This is a great look on you and the color is beautiful!

  5. Noelle
    June 11, 2021 / 2:46 pm

    I’d either be too hot or too cold in this outfit— goose bumps on my knees or a heat rash on my face. You look lovely, but it would never work for me.

  6. Erika
    June 11, 2021 / 2:45 pm

    This outfit looks great on you, but I dress very casually. I live near you and with our hot weather from May-October, I wouldn’t be able to wear a blazer. I find the blogs I read have clothing that is often too warm for 100 degree weather. I love your style!

    • Kelly
      June 16, 2021 / 7:44 am

      I find Erika’s comment similar to my own thoughts. I love the look with the blazer, and since moving to Miami, I have been adding knee length shorts to my wardrobe (also viewing them in same sense as a skirt). What I continue to struggle with is how to get that polished, pulled-together look without layering. I’m a midwest native so until temps drop below 70, I’d have to pass on the blazer. Layering seems to be the usual suggestion for completing a look given from the blogs, so if anyone has other suggestions, please shout them out!

      • Jennifer
        June 16, 2021 / 11:46 pm

        Accessories are one of the best ways. Earrings and bracelets are cooler than necklaces. Try a metallic bag and/or sandal. Remember to try belts and possibly a small scarf tied on the handle if you’re purse. These little details work wonders to look polished.

  7. Lin
    June 11, 2021 / 1:59 pm

    Love the blazer with the shorts.
    Takes me back a few years ago when I had a calico print blazer and short suit.
    I loved that outfit. It was so vestal. Just classy enough to ware for dinner, work or whatever.
    The Kate Spade bag would have looked perfect with my retro outfit.
    Love the bag, shoes and whole outfit

  8. Kay
    June 11, 2021 / 12:50 pm

    I can’t quite reconcile myself to dressy on top and beach on the bottom. I think it’s another of those mother-in-my-head voices that will not stop talking!

  9. Eve
    June 11, 2021 / 12:18 pm

    I think it depends on where you live. Certainly you could wear this look to any restaurant on the Coast. They are used to tourists walking in and out in shorts so it would like nice. We have casinos here that have entertainment as in circus shows, big name acts, comedians. So, wearing this outfit to a show would be fine. It’s too hot to keep the jacket on outside however.

  10. Audrey
    June 11, 2021 / 10:56 am

    Love the outfit. I wear the long shorts for summer, crops don’t look good since I am 5’2″.
    I bought skorts at Talbot’s because they had petite and misses lengths.

    • Jennifer
      June 11, 2021 / 10:46 pm

      Thanks Audrey

  11. Kathyh
    June 11, 2021 / 10:27 am

    Attractive shorts outfit. I wore similar linen shorts and blazers in the nineties when I was working here in Florida. I would never wear the outfit here now because it’s so hot. When I wear shorts, I do so to be casual whether its lunch with friends, picnic at the beach, etc. In that case, I wear nice shorts, sleeveless blouse in summer. When I dress up, I wear a dress or pants.

  12. Libda
    June 11, 2021 / 9:19 am

    This is a lovely outfit!!!! I would love wearing it for sure!

    Where did you get that purse from? I like it too! You always come through with dressing up an outfit to make it look stylish! I appreciate your ideas!

    I hope you finally found the right Dentist for you and that you will shortly be pain free!

    • Jennifer
      June 11, 2021 / 10:44 pm

      Thanks Linda. I think that one crown is finally finished but I have a few more that need repairing. It never seems to end.

  13. Laura Rutledge
    June 11, 2021 / 9:15 am

    It looks cute on you, and is a nice look if you need to dress up. I rarely do. I need to look nice for my day with dogs, horses, grand boy, gardening, hiking, construction site and perhaps 100 degree heat. I would appreciate a post on clothing for mature women that looks good and put together, that will stand up to an active, perhaps even dirty lifestyle, to help us feel confident too?

    • Jennifer
      June 11, 2021 / 10:43 pm

      Please tell me more about what you have in mind.

      • Nancy
        June 12, 2021 / 12:11 am

        This is how you wear shorts in a way that is pure class. Love your whole look. Sometimes these longer shorts look better on a petite than crops or capris. You nailed it.

      • Jennifer
        June 12, 2021 / 6:45 am

        Thank you, Nancy. I love this look.

  14. Suzanne Herder
    June 11, 2021 / 8:48 am

    Smart and classic outfit! Love how the round handbag complements the straight column of the outfit.

  15. MRSBEN2
    June 11, 2021 / 8:44 am

    Looking amazing, Jennifer! As to blazers; living in the great white North as I do they have always been a seasonal staple in my wardrobe and have several styles (from structured to over-sized) that I pair with many other garments. To conclude; I think a lot women shy away from them feeling they are too corporate in appearance but IMHO they add an edge and polished look which you have just proven, giving reason why I personally prefer them over a cardigan sweater …. ☺. Loving your vintage handbag. -Brenda-
    P.S.: Yes have worn a blazer with my only pair of shorts that I currently own and as to a skort you might find something in women’s golfing attire that would work for you.

    • Jennifer
      June 11, 2021 / 10:41 pm

      Thank you, Brenda! I hadn’t thought of golf attire. Brilliant idea.

  16. Nancy
    June 11, 2021 / 8:37 am

    The aqua blazer looks so nice with the shorts and your column of white. I bought the white linen blazer when you featured that, but I normally don’t wear blazers, or sweaters for that matter, in the summer. It’s just too hot, linen or not! I think I’d be more into blazers if I still worked. As far as shorts, I do wear them on occasion and I like to dress up, so I like this look. My normal go to in the summer is/are capris or pedal pushers rather than shorts. They would probably look nice with a blazer too.

  17. Donna
    June 11, 2021 / 7:49 am

    Looks nice together, but too hot in Texas in summer. I don’t look good in shorts at my age, but I used to wear them when younger before there were capris and crops. I hope capris never go out , as it has been so nice for older women with aging legs.

  18. Sally
    June 11, 2021 / 7:37 am

    Very smart outfit, but at my age I would prefer shorts just covering the knee. Possible?

    • Jennifer
      June 11, 2021 / 10:40 pm

      Yes! There is no end to the options for you this year. Pedal pushers are just below the knee and very popular.

  19. Celia Bass
    June 11, 2021 / 7:31 am

    I distinctly remember the trend to wear blazers with long shorts it seems not too, too long ago, but I’m old so maybe longer than other readers remember. Unfortunately, I gave away my trove of blazers that had rolled up sleeves , thinking they were out of fashion. Dumb me…should have known that trend would circle around again. You look lovely, and really cool in your outfit of light colors.

    • Linda P
      June 11, 2021 / 8:24 am

      Yes, they were called ‘city shorts.’ I was teaching school then and a few teachers wore them, but I don’t think the administrators were keen on the idea. The trend didn’t last very long.

    • Jennifer
      June 11, 2021 / 10:38 pm

      I remember it too, Celia. Everything always circles back around.

  20. Sue H
    June 11, 2021 / 7:26 am

    I love column dressing – it’s one of my go-tos. Always looks chic and pulled together. Aqua and white are such a wonderful combination for summer. Your look is easy-breezy!

    Looking forward to today’s IG chat.

    • Jennifer
      June 11, 2021 / 10:36 pm

      I’m loving the Aqua and white too

  21. Jan
    June 11, 2021 / 7:21 am

    Each detail of your ootd comes together to create an amazing, summery style that will take you just about anywhere! I am taking note and will try something similar with my new sage capris. I know I’ve said it before but to have the visual of a gorgeous style makes it so much easier for me to adapt it to my personal wardrobe. All the colors go so well together and the accessories are spot on!
    Fun, fun and more fun!

    • Jennifer
      June 11, 2021 / 10:34 pm

      Happy Friday Jan!

  22. Linda L
    June 11, 2021 / 7:08 am

    Before I moved to SoCal I didn’t own one pair of shorts but now I have several. They are very popular here and a nice update to crops. At almost 5’6 (and a month shy of 70) I have found the cut that hits right above my knee to be most flattering. Talbots calls it their Bermuda short & they’re a great fit for me. I dress them up with a fancy blouse but minus the blazer. Just way too hot here for a jacket. Try Talbots skorts; I find them to be a bit longer. I wear them running errands, golfing and just every day wear.

    • Jennifer
      June 11, 2021 / 10:33 pm

      Thanks Linda. I’ll give them a try

  23. Diane B
    June 11, 2021 / 7:02 am

    Great look with the blazer. The colour with the white is perfect for any sort of outing and suits you so well. That purse was a fabulous find and has stood up well. Looking forward to the skin care chat.

    • Jennifer
      June 11, 2021 / 7:06 am

      It was a treasure when I found it and I’ve alway taken impeccable care of it so I can use it for many years to come.

  24. Dianne
    June 11, 2021 / 6:48 am

    Beautiful outfit! Never thought to dress up shorts with a blazer. So classy. Have a wonderful weekend Jennifer

  25. Bea
    June 11, 2021 / 5:35 am

    Jennifer, this is a winner of an outfit. It inspires me to wear my blazers more often. Sometimes I forget that blazers look great with jeans and other casual bottoms. Instead of a sweater or a casual jacket, I will consider one of my blazers the next time I go somewhere that requires a cover-up for comfort. Thank you!

  26. millie whitehead
    June 11, 2021 / 5:34 am

    Like the ballet flats, but much too pricey!

    • Jennifer
      June 11, 2021 / 7:05 am

      I’ve included other flats in the shopping widget that may fit your budget better.

  27. Paulette Levy
    June 11, 2021 / 5:19 am

    As always, so very smart- a great look! I love the Aqua and with the white column, you look taller too. The touch of metallic (platinum shoe) adds a dressy feel too.
    Love it!

  28. Janice
    June 11, 2021 / 5:18 am

    I love the long shorts they look wonderful on you and the entire outfit works perfectly. I have purchased the shorts in black and white they look great and feel comfortable in any situation.

  29. Gwen Martin
    June 11, 2021 / 5:09 am

    Love the look. Love the idea of the blazer but here in the south there’s no way to wear a blazer outside. You would roast or melt. I can see carrying it with you and putting it on just before you enter a building with cold air conditioning.

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